Method of regulating the growth of plants

Abstract

Novel method for regulating the growth of plants which method comprises applying to the plants or their habitat, effective amounts of heterocyclic compound of the formula ##STR1## in which R 1 is alkyl or optionally substituted aryl, R 2 is hydrogen, alkyl or optionally substituted aryl, R 3 is hydrogen or the radical ##STR2## in which Y is oxygen or sulfur and R 5 is alkyl, haloalkyl, alkoxyalkyl, aryloxyalkyl, which is optionally substituted in the aryloxy part, alkoxy, optionally substituted aryl, optionally substituted aryloxy, monoalkylamino, dialkylamino, alkenylamino, dialkenylamino, optionally substituted arylamino, a 5-membered to 7-membered heterocyclic ring, bonded via nitrogen, or the radical ##STR3## in which R 6 is hydrogen or alkyl and R 7 is hydrogen or alkyl, or R 6 and R 7 , together with the adjacent nitrogen atom, are a 5-membered to 7-membered heterocyclic ring, R 4 is cyano or the grouping --COR 8 in which R 8 is alkoxy or amino, and X is oxygen or sulfur.

What is claimed is: 
     
       1. Method for regulating the growth of plants which method comprises applying to the plants or their habitat, effective amounts of a heterocyclic compound of the formula ##STR93## in which R 1  is alkyl of up to 6 carbon atoms, aryl of 6 on 10 carbon atoms or substituted aryl carrying at least one substituent selected from halogen, alkyl of up to 4 carbon atoms, haloalkyl of to 4 carbon atoms, alkoxy of up to 4 carbon atoms, alkylthio of up to 4 carbon atoms, alkylsulfonyl of up 4 carbon atoms and nitro; R 2  is hydrogen, alkyl of up to 6 carbon atoms, aryl of 6 or 10 carbon atoms, or substituted aryl having at least one substituent selected from halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms and nitro,   R 3  is hydrogen or the radical ##STR94##  in which Y is oxygen and R 5  is alkyl with 1 to 6 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxyalkyl with 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms in the alkoxy part, aryloxyalkyl, which has 6 or 10 carbon atoms in the aryloxy part and 1 to 4 carbon atoms in the alkyl part and optionally carrying one or more substituents on the aryloxy part selected from halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms; alkoxy with 1 to 4 carbon atoms; aryl with 6 or 10 carbon atoms, substituted aryl carrying one or more substituents selected from halogen, alkyl with 1 to 4 carbon atoms or haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy, alkylthio, and alkylsulphonyl with 1 to 4 carbon atoms and nitro; aryloxy with 6 or 10 carbon atoms substituted aryloxy having at least one substituent selected from halogen, alkyl with 1 to 4 carbon atom, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy, alkylthio, alkylsulphonyl with 1 to 4 carbon atoms and nitro; monoalkylamino with 1 to 4 carbon atoms; dialkylamino with 1 to 4 carbon atoms in each alkyl group; alkenylamino with up to 4 carbon atoms; dialkenylamino with up to 4 carbon atoms in each alkenyl group; arylamino with 6 or 10 carbon atoms substituted arylamino carrying one or more substituents selected from halogen, alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms, alkoxy with 1 to 4 carbon atoms, alkylthio with 1 to 4 carbon atoms, alkylsulphonyl with 1 to 4 carbon atoms and nitro R 4  is cyano or the grouping -COR 8  in which R 8  is alkoxy or amino, and   X is oxygen or sulfur.       
     
     
       2. Method as claimed in claim 1 wherein R 1  is alkyl of up to 4 carbon atoms. 
     
     
       3. Method as claimed in claim 1 wherein R 1  is optionally substituted aryl of 6 or 10 carbon atoms in the aryl moiety. 
     
     
       4. Method as claimed in claim 1 wherein R 2  is hydrogen. 
     
     
       5. Method as claimed in claim 1 wherein R 2  is alkyl of 1 to 4 carbon atoms. 
     
     
       6. Method as claimed in claim 1 wherein R 2  is optionally substituted aryl of from 6 or 10 carbon atoms in the aryl moiety. 
     
     
       7. Method as claimed in claim 1 wherein R 3  is hydrogen. 
     
     
       8. Method as claimed in claim 1 wherein R 3  is the radical ##STR95## 
     
     
       9. Method as claimed in claim 8 wherein Y is oxygen. 
     
     
       10. Method as claimed in claim 8 wherein R 5  is alkyl, haloalkyl or alkoxyalkyl of from 1 to 4 carbon atoms per alkyl moiety. 
     
     
       11. Method as claimed in claim 8 wherein R 5  is aryloxyalkyl optionally substituted in the aryloxy moiety and having from 6 or 10 carbon atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety. 
     
     
       12. Method as claimed in claim 8 wherein R 5  is alkoxy of up to 4 carbon atoms. 
     
     
       13. Method as claimed in claim 8 wherein R 5  is optionally substituted aryl or aryloxy of from 6 or 10 carbon atoms in the aryl moiety. 
     
     
       14. Method as claimed in claim 8 wherein R 5  is monoalkylamino, dialkylamino, alkenylamino, or dialkenylamino with up to 4 carbon atoms per alkyl or alkenyl moiety. 
     
     
       15. Method as claimed in claim 8 wherein R 5  is optionally substituted arylamino of from 6 or 10 carbon atoms in the aryl moiety. 
     
     
       16. Method as claimed in claim 1 wherein R 4  is cyano. 
     
     
       17. Method as claimed in claim 1 wherein R 4  is the radical -COR 8 . 
     
     
       18. Method as claimed in claim 17 wherein R 8  alkoxy of up to 4 carbon atoms. 
     
     
       19. Method as claimed in claim 17 wherein R 8  is amino. 
     
     
       20. Method as claimed in claim 1 wherein X is oxygen. 
     
     
       21. Method as claimed in claim 1 wherein X is sulfur. 
     
     
       22. Method as claimed in claim 1 wherein said compound is 2-amino-3-ethoxycarbonyl-4-methyl-5-phenylthiophene. 
     
     
       23. Method as claimed in claim 1 wherein said compound is 2-amino-ethoxycarbonyl-4,5-dimethyl-thiophene. 
     
     
       24. Method as claimed in claim 1 wherein said compound is 2-benzoylamino-3-cyano-4-tert.butyl-thiophene. 
     
     
       25. Method as claimed in claim 1 wherein said compound is 2-(2,4,5-trichlorophenoxymethylcarbonyl)-amino-3-cyano-4-tert.butyl-furane 
     
     
       26. Method as claimed in claim 1 wherein said compound is 2-(2,4,5-trichlorophenoxymethylcarbonyl)-amino-3-cyano-4,5-diphenyl-furane. 
     
     
       27. Method as claimed in claim 1 wherein said compound is 2-propionylamino-3-cyano-4-tert.-butyl-furane. 
     
     
       28. Method as claimed in claim 1 wherein said compound is selected from 2-amino-3-ethoxycarbonyl-4-methyl-5-phenyl-thiophene, 3-ethoxycarbonyl-4,5-dimethylthiophene, 2-benzoylamino-3-cyano-4-tert.-butyl-thiophene, 2-(2,4,5-trichlorophenoxymethylcarbonyl)-amino-3-cyano-4-tert.-butyl-furane, 2-(2,4,5-trichlorophenoxymethylcarbonyl)-amino-3-cyano-4,5-diphenyl-furane and 2-propionylamino-3-cyano-4-tert.-butyl-furane.